I’m writing you today from the south of France, where I’ve been taking a little breather before a busy fall. This episode is a reflection on some of the most popular questions that came up around the launch of Never Play It Safe. In the particular lies the universal — and the questions from our community reflect challenges so many of us face.

Matt asked about starting a coaching/consulting side hustle. My answer? Don’t try to solve everything from the couch. Start small. Run tiny experiments. Serve people by solving the problems you’ve already solved for yourself.
From there, Dylan jumped in with a question about making a film project with a comedian friend. We dug into what it means to treat creative collaborations like real businesses — agreements, responsibilities, financing, and the all-important element of play.

• Side hustles that stick: why solving your own past problems makes you a better coach or consultant
• Tiny experiments: the fastest way to test ideas and get real data instead of planning forever
• Collaboration as play: how operating agreements and clear roles keep partnerships fun instead of frustrating
• Burnout recovery: why rediscovering play is the antidote to grazing through work like a cow instead of hunting like a lion

The big idea? The best way forward isn’t overthinking — it’s showing up, experimenting, and rediscovering play in the process.

At the height of my career—awards, startups, celebrity collabs—my wife stopped me cold with one question: “How much is enough?”
I didn’t have an answer. From the outside, life looked perfect. But inside, I was chasing “more” without knowing why.

The culture around us says: keep climbing, keep grinding, keep stacking. But more for the sake of more eventually costs you—your health, your relationships, even your sense of self. Without defining what “enough” looks like, ambition becomes a treadmill you can’t step off.

Here’s the twist: constraints aren’t limitations, they’re freedom.
When you know what’s enough—whether that’s money, recognition, or time—you can stop running in every direction and start building the life you actually want.

• The trap of “more”: why unchecked ambition always demands a bigger price
• Defining enough: how boundaries create focus, energy, and freedom
• Hustle vs. challenge: the difference between busy work and meaningful growth

The big idea? If you don’t define your “enough,” the world will do it for you—and you probably won’t like the result. Ask the question. Write it down. Revisit it often. That’s how you turn ambition into a compass instead of a trap.

If social media feels heavier than it used to, you’re not imagining it. Infinite feeds, algorithm whiplash, and the pressure to post “one more thing” can drain the very creativity we’re trying to share. Here’s the shift: treat social media like a stage you step onto with intent—not a sofa you collapse into by default.

A stage has purpose: you arrive prepared, you deliver, you connect, you step off. A sofa invites scrolling, numbing, and losing track of the most precious resource you own—your attention. When you design systems that honor the stage, you get 90% of the upside with a fraction of the noise.

Create before you consume. Get your ideas out of your head and into the world first. Then study the landscape with clear eyes: What worked? What didn’t? What can you improve next rep?

• Systems resist their systems: your schedule, not the algorithm, sets when and how you show up
• Frameworks, not feeds: reusable prompts and formats that make creation repeatable
• Stagecraft: show up to present, connect, and move the ball forward—then step off

The big idea?
Social platforms are powerful—when they serve your purpose. Use them as a stage: step on with intention, deliver your best, connect with your people, and step off before the sofa starts calling your name. For the full playbook—including how to set boundaries that stick—check out this week’s episode of the show.